Triethylamine → 5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide

HRID 1774849Notes

Reaction equation

HRID 1774849 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:11][O:12][NH:13][CH3:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:13]([O:12][CH3:11])[CH3:14])=[O:8]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 887075-Bromonicotinic acid

Product 1

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-nicotinic acid (2.02 g, 10 mmol) and O,N-dimethyl-hydroxylamine (670 mg, 11 mmol) in DMF (100 mL) was added HOBt (400 mg, 0.3 mmol), EDCI (2.09 g, 11 mmol) and Et3N (1.11 g, 11 mmol). The resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and it was extracted with EtOAc. The organic layer was washed with brine, dried by anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was then purified by flash chromatography to give the title compound (2.08 g, 85%) as a solid.

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried by anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by flash chromatography

Sources & evidence

ORD record
ord-16c6519f4ad04165b57bf323f83ff95f
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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